15. Tara Reid
Source: Iconosquare
Tara Reid is an actress. She used to be a very famous actress, although recently she hasn’t had as many different roles as she had previously. When it comes to the athletes she has dated, she has had a number of different famous athletes that she has had relationships with. She dated the NFL players Tom Brady during 2002, Jeremy Shockey during 2003, and Kyle Boller during 2004. She also dated NHL player Sergei Fedorov from 2004 to 2005 and the Australian tennis player Mark Philippoussis.